It is risky for technologists to ignore the non-technical context in which their systems will be deployed, just as it is risky for policy makers to ignore the limits and potential of technology. Yet such insularity is all too common. The results are unfortunate but not surprising. This lecture explores the structure dialogs take to bring about what might be termed "security failings" by revisiting: identity theft, electronic voting, digital right management, and the overall vulnerabilities of today's deployed software.